Hi @Adam Cohen
First, can you please provide your Outlook version? I am using the latest version which is 16.107.3 and I notice some of behavior:
When you open Search, All Items is selected and the highlighted part is greyed out, you will get 15 conditions. What you can do now is switch back to Current folder, let the highlighted part no longer greyed out, and click Close Search.
The next time you open, all 29 conditions will be back.
In conclusion, when you first open Search in upper right corner, if the highlighted part is greyed out, 15 conditions.
If you want to use 29 conditions in All items, you will need to switch back to Current Folder, close Search, open Seach again and select All items.
Please try and let me know if you see the same behavior.
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